Breaking Sales

Why do sales professionals avoid the questions that matter most? Sometimes it's because every conversation starts to feel like a verdict on who they are.

In this episode, Dan sits down with Elizabeth Weingarten, a journalist, applied behavioral scientist, and author of How to Fall in Love with Questions. They explore what's behind the inability to ask good questions, and how it most often starts with the question we are asking ourselves. They also get into what kind of questions prospects and clients are asking themselves before and after meeting with you.

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The same drive that gets you into the conversation can sabotage you once you're in it.

That's one of seven behaviors Dan and Pam have consistently seen in the highest performers they've coached, many of them earning seven figures a year. Some will sound familiar. Some won't. And one might change how you react the next time a prospect tells you the conversation is going well.

I rechecked every line against the transcript, and nothing else overlaps. The only exception is "seven figures," which is unavoidable since it's the episode's premise.

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If you're in sales, you may have noticed a familiar pattern: a hard question you soften before you ask it, a prospecting call you keep pushing out to tomorrow, or an observation you don't make because saying it feels risky. It's easy to chalk these behaviors up to busyness or a lack of discipline. Usually, the root cause is something else entirely.

In this episode, Dan sits down with Dr. Jason Moser, a clinical psychologist and researcher at Michigan State University, to talk about what's actually happening in those moments, and why avoiding them tends to make things worse, not better. If discomfort has ever talked you out of doing something you knew you should do, you won't want to miss this episode.

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Sales professionals can spend enormous energy making sure a prospect understands their value, and it still isn't enough to move the deal. In this episode, Dan and Pam explore why that happens, and why demonstrating value is the wrong focus entirely. A prospect's brain reacts to change the same way it reacts to any perceived threat — and without a reason to think past the present moment, staying where they are will always feel safer than making a change. If you've ever been tempted to lean harder on your value or expertise when a deal started to stall, this episode is for you.

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What if the thing holding back your performance isn't a problem with your abilities, but with how you think about the moments you're dreading?

The outreach you avoid, the questions you hesitate to ask, the "no" you're bracing for before you pick up the phone — these are all examples of how your brain is wired to focus on what could go wrong instead of what could go right. But there's a skill that can help you change how you think about these situations: cognitive reframing.

In this episode, Dan sits down with Ayelet Fishbach, a motivation scientist at the University of Chicago and author of Get It Done: Surprising Lessons from the Science of Motivation, to discuss why the path to any goal feels the way it does — and how to reframe the setbacks you encounter along the way.

This conversation is relevant to anyone working towards a goal that takes sustained effort over time — particularly salespeople who face regular rejection as part of the job and are looking for better ways to manage it.

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Prospects don't enter sales conversations with a blank slate. They bring years of experiences, assumptions, loyalties, and fears that shape how they evaluate every option in front of them. Those biases influence the prospects willingness to change and how they filter your ability to help them change.

In Part Two of their conversation, I and Pam explore why trying to convince someone they're wrong often strengthens the very beliefs you're trying to change. We discuss how, instead, great sales professionals create the kind of conversation that helps prospects examine those beliefs for themselves.

If you've ever walked away from a meeting knowing your solution was the better choice—but still lost the opportunity—this episode will help you understand what kind of questions you'll need to ask to help your prospect minimize the impact of negative biases.

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You probably don't think of yourself as resistant to change. But when something has worked for you before, it's easy to assume that's the reason for your success — and that habit makes it hard to notice when a different approach might actually work better. In this episode, Dan sits down with cognitive scientist, author, and former professional poker player Annie Duke. Together they explore what's really going on when someone won't let go of an approach that's not serving them — whether that's a sales professional or a prospect — and what it takes to move past it.

If you've ever struggled to get a decision-maker to consider something new or held onto a deal that was dead a long time ago, this episode is for you.

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The opening minutes of a prospect meeting carry more weight than many sales professionals give them credit for. It can dictate whether you are starting from a position of strength or from behind. From that very first moment forward the prospect is trying to determine one thing: What does this person actually want from me?

The question is - do you want your prospects thinking about where you're trying to take them, or how you will use their answers to advance a sale? Or do you want their energy and effort focused on answering your questions with honesty? All of this is determined by how you start your conversations.

In this episode, Dan and Pam explore what it actually takes to create the conditions for an honest conversation — including what's required to help prospects examine their biases and challenge their beliefs.

This episode is relevant for anyone who has walked out of a meeting thinking it went fine — and then never heard back.

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There is a pattern that often appears in sales organizations: someone isn't performing, and the response is frustration, blame, or eventually, a conversation about whether they still belong on the team. What rarely happens is an honest look at whether that person was ever actually set up to succeed — whether they had the development, environment, and preparation to perform when the stakes were high.

In the 200th episode of Breaking Sales, Dan sits down with three-time national championship-winning college football coach Urban Meyer for a conversation about what high performance actually requires. Coach Meyer spent decades putting other people in positions to succeed. His philosophy on what that takes — and what gets in the way — translates directly to how you lead the people around you… and how you think about your own performance.

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There's a reason so many smart, capable sales professionals consistently avoid doing the things they know they need to do and taking the risks they know they need to take. It's not laziness, and it's not a lack of motivation.

As it turns out, it's rooted in something far more fundamental about how the human mind works. Roy Baumeister is a decorated social psychologist who has spent decades researching topics like loss aversion, self-control, and the outsized weight of negative experiences. In this episode, Roy joins Dan for a conversation that digs into why it's so tempting to pull back in the moments that matter most — as well as what it takes to start overriding that urge.

If you've ever found yourself consistently avoiding the things you know matter most, this episode is for you.

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